2-Aminobenzaldehyde

2-Aminobenzaldehyde Basic information
Description Physical properties Uses Preparation Reference
Product Name:2-Aminobenzaldehyde
Synonyms:Benzaldehyde,2-amino-;2-Aminobenzaldeyhde;o-Amino Benzaldehyde 2-Amino Benzaldehyde;ORTHO-AMINOBENZALDEHYDE;2-AMINOBENZALDEHYDE;2-AMinobenzaldehyde >=98%;2-Formylaniline;Bromhexine Impurity 11
CAS:529-23-7
MF:C7H7NO
MW:121.14
EINECS:208-454-3
Product Categories:Carbonyl Compounds;Aldehydes;C7
Mol File:529-23-7.mol
2-Aminobenzaldehyde Structure
2-Aminobenzaldehyde Chemical Properties
Melting point 38°C
Boiling point 225.84°C (rough estimate)
density 1.1344 (rough estimate)
refractive index 1.5323 (estimate)
Fp 113 °C
storage temp. -20°C
form Low Melting Solid
pka-0.01±0.10(Predicted)
color White to yellow
Stability:Unstable: reported to polymerize rapidly at room temperature. Incompatible with strong oxidizing agents, strong bases. Store at -20 C.
LogP1.080 (est)
CAS DataBase Reference529-23-7(CAS DataBase Reference)
NIST Chemistry Reference2-Aminobenzaldehyde(529-23-7)
EPA Substance Registry SystemBenzaldehyde, 2-amino- (529-23-7)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-37/39-36
WGK Germany 3
8-10-23
HS Code 29223990
MSDS Information
ProviderLanguage
SigmaAldrich English
2-Aminobenzaldehyde Usage And Synthesis
Description2-Aminobenzaldehyde is one of the three isomers of aminobenzaldehyde. It is used as a versatile substrate for rhodium-catalyzed alkyne hydroacylation.1 It is used to prepare quinoline derivatives as antiviral agents, electroluminescent materials for OLEDs, and 2-tosylaminopheyl cyclopropylmethanols for gold-catalyzed cyclopropyl carbinol rearrangement. It is also used for the Friedländer-type synthesis, the benzyl C-H bond amination of acrymethylamines catalyzed by hydroxy-TEMPO, and for silver-catalyzed aniline mediated cascade hydroamination/cycloaddition reactions.
Physical properties2-Aminobenzaldehyde has recently been identifed as an important component in the fragrant scents of many flowers. These flowers include broom (Spartium junceum), false acacia (Robinia pseudoacacia), European bird cherry (Padus avium), ily (Lilium candidum), seringat (Philadelphus coronarius), Pittosporum tobira, Hypecoum imberbe, and H. fragrant. This chemical is also responsible for the“"sweet" or fragrant odor of the wild mushroom Hebeloma sacchariolens.
UsesReactant for:
Preparation of quinoline derivatives as antiviral agents
Preparation of electroluminescent materials for OLEDs
Friedlander-type synthesis
Preparation of 2-tosylaminophenyl cyclopropylmethanols for gold-catalyzed cyclopropyl carbinol rearrangement
Benzyl C-H bond amination of arylmethylamines catalyzed by hydroxy-TEMPO
Silver-catalyzed aniline mediated cascade hydroamination/cycloaddition reactions





Preparation2-Aminobenzaldehyde is prepared by reduction of 2- nitrobenzaldehyde with aqueous ferrous sulfate and ammonia. Since the product contains both aldehyde and amino groups it polymerizes easily. This means that it must be isolated rapidly after it forms, which is done by steam distillation of the product from the reaction mixture.
ReferenceM. Castaing, S. L. Wason, B. Estepa, J. F. Hooper, M. C. Willis, 2‐Aminobenzaldehydes as Versatile Substrates for Rhodium‐Catalyzed Alkyne Hydroacylation: Application to Dihydroquinolone Synthesis, Angewandte Chemie, 2013, vol. 52, pp. 13280-13283
Chemical Propertieslight yellow crystalline powder
UsesReactant for:
  • Preparation of quinoline derivatives as antiviral agents
  • Preparation of electroluminescent materials for OLEDs
  • Friedlander-type synthesis
  • Preparation of 2-tosylaminophenyl cyclopropylmethanols for gold-catalyzed cyclopropyl carbinol rearrangement
  • Benzyl C-H bond amination of arylmethylamines catalyzed by hydroxy-TEMPO
  • Silver-catalyzed aniline mediated cascade hydroamination/cycloaddition reactions
Purification MethodsDistil it in steam and recrystallise it from H2O or EtOH/ Et2O. The semicarbazone has m 247o. [Beilstein 14 H 21, 14 I 356, 14 II 14, 14 III 47, 14 IV 42.]
4-Aminobenzaldehyde phenyl hydrazone OIL BLUE N 2-AMINOBENZALDEHYDE-ETHYLENE-DIIMINE ACID VIOLET 34 4-AMINOBENZALDEHYDE,P-AMINOBENZALDEHYDE REACTIVE BLACK 5 Solvent Green 3 Acid Green 25 4-(N-Ethyl-2-cyanoethylamino)benzaldehyde Disperse Red 9 o-Aminophenylacetic acid 2-Chloro-N-[4-chloro-2-(2-chlorobenzoyl)phenyl]acetamide Disperse Blue 3 Benzaldehyde, 4-(2-chloroethyl)ethylamino-, polymer with 2,3-dihydro-1H-pyrrolo1,2-abenzimidazole and 4-methylpyridine ACID BLUE 25 2-Methyl-4-[N-ethyl-N-(β-ethoxy)ethyl]aminobenzaldehyde Disperse Blue 14 ACID GREEN 27 (C.I. 61580)

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